JP2009542696A5

JP2009542696A5 -

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Publication number: JP2009542696A5
Authority: JP; Japan
Prior art keywords: inhibitor; group; substituted; alkyl; compound
Prior art date: 2007-07-06
Legal status : Granted

Application number

JP2009518393A

Other languages

English (en)

Japanese (ja)

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JP4881433B2 (ja

JP2009542696A (ja

Filing date

2007-07-06

Publication date

2011-02-17

2007-07-06 Application filed filed Critical

2007-07-06 Priority claimed from PCT/US2007/015604 external-priority patent/WO2008010921A2/en

2009-12-03 Publication of JP2009542696A publication Critical patent/JP2009542696A/ja

2011-02-17 Publication of JP2009542696A5 publication Critical patent/JP2009542696A5/ja

2012-02-22 Application granted granted Critical

2012-02-22 Publication of JP4881433B2 publication Critical patent/JP4881433B2/ja

Status Active legal-status Critical Current

2027-07-06 Anticipated expiration legal-status Critical

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150000001875 compounds Chemical class 0.000 claims description 613
125000000623 heterocyclic group Chemical group 0.000 claims description 282
230000002401 inhibitory effect Effects 0.000 claims description 282
125000000217 alkyl group Chemical group 0.000 claims description 269
239000003112 inhibitor Substances 0.000 claims description 255
239000000203 mixture Substances 0.000 claims description 197
125000002947 alkylene group Chemical group 0.000 claims description 174
125000003118 aryl group Chemical group 0.000 claims description 173
-1 3-chloro-2-fluorobenzyl Chemical group 0.000 claims description 164
239000003814 drug Substances 0.000 claims description 155
229940079593 drugs Drugs 0.000 claims description 99
241000580858 Simian-Human immunodeficiency virus Species 0.000 claims description 93
125000000547 substituted alkyl group Chemical group 0.000 claims description 89
125000001072 heteroaryl group Chemical group 0.000 claims description 84
150000002148 esters Chemical class 0.000 claims description 83
239000011780 sodium chloride Substances 0.000 claims description 80
125000001424 substituent group Chemical group 0.000 claims description 79
239000012453 solvate Substances 0.000 claims description 77
150000003839 salts Chemical class 0.000 claims description 75
239000002777 nucleoside Substances 0.000 claims description 70
150000003833 nucleoside derivatives Chemical class 0.000 claims description 69
125000003710 aryl alkyl group Chemical group 0.000 claims description 64
125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 63
125000004452 carbocyclyl group Chemical group 0.000 claims description 60
125000004404 heteroalkyl group Chemical group 0.000 claims description 60
101700033252 ALT2 Proteins 0.000 claims description 58
101710025897 ASPCADRAFT_517149 Proteins 0.000 claims description 57
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102000033147 ERVK-25 Human genes 0.000 claims description 55
230000001225 therapeutic Effects 0.000 claims description 53
108010092799 EC 2.7.7.49 Proteins 0.000 claims description 51
229910052757 nitrogen Inorganic materials 0.000 claims description 49
125000005418 aryl aryl group Chemical group 0.000 claims description 48
229910052739 hydrogen Inorganic materials 0.000 claims description 42
125000003107 substituted aryl group Chemical group 0.000 claims description 38
125000005842 heteroatoms Chemical group 0.000 claims description 36
239000008194 pharmaceutical composition Substances 0.000 claims description 33
230000035633 Metabolized Effects 0.000 claims description 31
102100012080 CCR5 Human genes 0.000 claims description 30
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IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical class N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-AFCXAGJDSA-N 0.000 claims description 29
125000004103 aminoalkyl group Chemical group 0.000 claims description 28
ZIUSSTSXXLLKKK-HWUZOJPISA-N Curcumin Natural products C1=C(O)C(OC)=CC(\C=C\C(\O)=C/C(=O)/C=C/C=2C=C(OC)C(O)=CC=2)=C1 ZIUSSTSXXLLKKK-HWUZOJPISA-N 0.000 claims description 27
QAIPRVGONGVQAS-DUXPYHPUSA-N caffeic acid Natural products OC(=O)\C=C\C1=CC=C(O)C(O)=C1 QAIPRVGONGVQAS-DUXPYHPUSA-N 0.000 claims description 27
239000002773 nucleotide Substances 0.000 claims description 23
125000003729 nucleotide group Chemical group 0.000 claims description 23
102100002212 CXCR4 Human genes 0.000 claims description 21
101710003734 CXCR4 Proteins 0.000 claims description 21
101700014732 GCS1 Proteins 0.000 claims description 21
108010050904 Interferons Proteins 0.000 claims description 21
102000014150 Interferons Human genes 0.000 claims description 21
239000000137 peptide hydrolase inhibitor Substances 0.000 claims description 21
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239000004030 hiv protease inhibitor Substances 0.000 claims description 20
229940079322 interferon Drugs 0.000 claims description 20
XQSPYNMVSIKCOC-NTSWFWBYSA-N (2R-cis)-4-amino-5-fluoro-1-(2-(hydroxymethyl)-1,3-oxathiolan-5-yl)-2(1H)-Pyrimidinone Chemical compound C1=C(F)C(N)=NC(=O)N1[C@H]1O[C@@H](CO)SC1 XQSPYNMVSIKCOC-NTSWFWBYSA-N 0.000 claims description 19
239000002253 acid Substances 0.000 claims description 19
GIXWDMTZECRIJT-UHFFFAOYSA-N Aurintricarboxylic acid Chemical compound C1=CC(=O)C(C(=O)O)=CC1=C(C=1C=C(C(O)=CC=1)C(O)=O)C1=CC=C(O)C(C(O)=O)=C1 GIXWDMTZECRIJT-UHFFFAOYSA-N 0.000 claims description 18
241000723343 Cichorium Species 0.000 claims description 18
235000007542 Cichorium intybus Nutrition 0.000 claims description 18
NHKZSTHOYNWEEZ-AFCXAGJDSA-N Taribavirin Chemical compound N1=C(C(=N)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 NHKZSTHOYNWEEZ-AFCXAGJDSA-N 0.000 claims description 18
229940074360 caffeic acid Drugs 0.000 claims description 18
235000004883 caffeic acid Nutrition 0.000 claims description 18
229960005107 darunavir Drugs 0.000 claims description 18
CJBJHOAVZSMMDJ-HEXNFIEUSA-N darunavir Chemical compound C([C@@H]([C@H](O)CN(CC(C)C)S(=O)(=O)C=1C=CC(N)=CC=1)NC(=O)O[C@@H]1[C@@H]2CCO[C@@H]2OC1)C1=CC=CC=C1 CJBJHOAVZSMMDJ-HEXNFIEUSA-N 0.000 claims description 18
239000003084 hiv integrase inhibitor Substances 0.000 claims description 18
KYRSNWPSSXSNEP-ZRTHHSRSSA-N (4R,5S,6S,7R)-1,3-bis[(3-aminophenyl)methyl]-4,7-dibenzyl-5,6-dihydroxy-1,3-diazepan-2-one Chemical compound NC1=CC=CC(CN2C(N(CC=3C=C(N)C=CC=3)[C@H](CC=3C=CC=CC=3)[C@H](O)[C@@H](O)[C@H]2CC=2C=CC=CC=2)=O)=C1 KYRSNWPSSXSNEP-ZRTHHSRSSA-N 0.000 claims description 17
RYMCFYKJDVMSIR-RNFRBKRXSA-N Apricitabine Chemical compound O=C1N=C(N)C=CN1[C@@H]1S[C@H](CO)OC1 RYMCFYKJDVMSIR-RNFRBKRXSA-N 0.000 claims description 17
XPOQHMRABVBWPR-ZDUSSCGKSA-N Efavirenz Chemical compound C([C@]1(C2=CC(Cl)=CC=C2NC(=O)O1)C(F)(F)F)#CC1CC1 XPOQHMRABVBWPR-ZDUSSCGKSA-N 0.000 claims description 17
102000015084 HIV Reverse Transcriptase Human genes 0.000 claims description 17
108010078851 HIV Reverse Transcriptase Proteins 0.000 claims description 17
239000003795 chemical substances by application Substances 0.000 claims description 17
229960003804 efavirenz Drugs 0.000 claims description 17
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OLROWHGDTNFZBH-XEMWPYQTSA-N Alisporivir Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](C(C)C)N(CC)C(=O)[C@@H](C)N(C)C1=O OLROWHGDTNFZBH-XEMWPYQTSA-N 0.000 claims description 16
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CZFFBEXEKNGXKS-UHFFFAOYSA-N Raltegravir Chemical compound O1C(C)=NN=C1C(=O)NC(C)(C)C1=NC(C(=O)NCC=2C=CC(F)=CC=2)=C(O)C(=O)N1C CZFFBEXEKNGXKS-UHFFFAOYSA-N 0.000 claims description 16
101710027357 SPAC3C7.13c Proteins 0.000 claims description 16
101710027351 SPCC794.01c Proteins 0.000 claims description 16
229960000517 boceprevir Drugs 0.000 claims description 16
LHHCSNFAOIFYRV-DOVBMPENSA-N boceprevir Chemical group O=C([C@@H]1[C@@H]2[C@@H](C2(C)C)CN1C(=O)[C@@H](NC(=O)NC(C)(C)C)C(C)(C)C)NC(C(=O)C(N)=O)CC1CCC1 LHHCSNFAOIFYRV-DOVBMPENSA-N 0.000 claims description 16
229910052736 halogen Inorganic materials 0.000 claims description 16
150000002367 halogens Chemical class 0.000 claims description 16
230000036231 pharmacokinetics Effects 0.000 claims description 16
MFDFERRIHVXMIY-UHFFFAOYSA-N Procaine Chemical group CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 claims description 15
QWAXKHKRTORLEM-UGJKXSETSA-N Saquinavir Chemical compound C([C@@H]([C@H](O)CN1C[C@H]2CCCC[C@H]2C[C@H]1C(=O)NC(C)(C)C)NC(=O)[C@H](CC(N)=O)NC(=O)C=1N=C2C=CC=CC2=CC=1)C1=CC=CC=C1 QWAXKHKRTORLEM-UGJKXSETSA-N 0.000 claims description 15
108010080374 albuferon Proteins 0.000 claims description 15
YIBOMRUWOWDFLG-ONEGZZNKSA-N rilpivirine Chemical compound CC1=CC(\C=C\C#N)=CC(C)=C1NC1=CC=NC(NC=2C=CC(=CC=2)C#N)=N1 YIBOMRUWOWDFLG-ONEGZZNKSA-N 0.000 claims description 15
229950006081 taribavirin Drugs 0.000 claims description 15
VKHAHZOOUSRJNA-GCNJZUOMSA-N Mifepristone Chemical compound C1([C@@H]2C3=C4CCC(=O)C=C4CC[C@H]3[C@@H]3CC[C@@]([C@]3(C2)C)(O)C#CC)=CC=C(N(C)C)C=C1 VKHAHZOOUSRJNA-GCNJZUOMSA-N 0.000 claims description 14
NCDNCNXCDXHOMX-XGKFQTDJSA-N Ritonavir Chemical compound N([C@@H](C(C)C)C(=O)N[C@H](C[C@H](O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1SC=NC=1)CC=1C=CC=CC=1)C(=O)N(C)CC1=CSC(C(C)C)=N1 NCDNCNXCDXHOMX-XGKFQTDJSA-N 0.000 claims description 14
230000001721 combination Effects 0.000 claims description 14
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229960000311 ritonavir Drugs 0.000 claims description 14
229940090438 Infergen Drugs 0.000 claims description 13
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125000002768 hydroxyalkyl group Chemical group 0.000 claims description 13
HLQXYDHLDZTWDW-KAWPREARSA-N (2R,4S,5R)-1-(4-tert-butyl-3-methoxybenzoyl)-4-(methoxymethyl)-2-(pyrazol-1-ylmethyl)-5-(1,3-thiazol-2-yl)pyrrolidine-2-carboxylic acid Chemical compound C([C@]1(C[C@@H]([C@@H](N1C(=O)C=1C=C(OC)C(=CC=1)C(C)(C)C)C=1SC=CN=1)COC)C(O)=O)N1C=CC=N1 HLQXYDHLDZTWDW-KAWPREARSA-N 0.000 claims description 12
FWKQNCXZGNBPFD-UHFFFAOYSA-N 1,4-dimethyl-7-(1-methylethyl)azulene Chemical compound CC(C)C1=CC=C(C)C2=CC=C(C)C2=C1 FWKQNCXZGNBPFD-UHFFFAOYSA-N 0.000 claims description 12
CBVCZFGXHXORBI-PXQQMZJSSA-N Indinavir Chemical compound C([C@H](N(CC1)C[C@@H](O)C[C@@H](CC=2C=CC=CC=2)C(=O)N[C@H]2C3=CC=CC=C3C[C@H]2O)C(=O)NC(C)(C)C)N1CC1=CC=CN=C1 CBVCZFGXHXORBI-PXQQMZJSSA-N 0.000 claims description 12
QAGYKUNXZHXKMR-HKWSIXNMSA-N Nelfinavir Chemical compound CC1=C(O)C=CC=C1C(=O)N[C@H]([C@H](O)CN1[C@@H](C[C@@H]2CCCC[C@@H]2C1)C(=O)NC(C)(C)C)CSC1=CC=CC=C1 QAGYKUNXZHXKMR-HKWSIXNMSA-N 0.000 claims description 12
229960001936 indinavir Drugs 0.000 claims description 12
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DZRQMHSNVNTFAQ-IVGJVWKCSA-N (2R,3R)-2,3-dihydroxybutanedioic acid;(2R,3S,4R,5S)-1-(6-ethoxyhexyl)-2-methylpiperidine-3,4,5-triol Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O.CCOCCCCCCN1C[C@H](O)[C@@H](O)[C@@H](O)[C@H]1C DZRQMHSNVNTFAQ-IVGJVWKCSA-N 0.000 claims description 11
AXRYRYVKAWYZBR-GASGPIRDSA-N Atazanavir Chemical compound C([C@H](NC(=O)[C@@H](NC(=O)OC)C(C)(C)C)[C@@H](O)CN(CC=1C=CC(=CC=1)C=1N=CC=CC=1)NC(=O)[C@@H](NC(=O)OC)C(C)(C)C)C1=CC=CC=C1 AXRYRYVKAWYZBR-GASGPIRDSA-N 0.000 claims description 11
208000005721 HIV Infections Diseases 0.000 claims description 11
229960003277 atazanavir Drugs 0.000 claims description 11
201000001820 human immunodeficiency virus infectious disease Diseases 0.000 claims description 11
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
NJBBLOIWMSYVCQ-VZTVMPNDSA-N Kynostatin 272 Chemical compound C([C@H](NC(=O)[C@@H](NC(=O)COC=1C2=CC=NC=C2C=CC=1)CSC)[C@H](O)C(=O)N1[C@@H](CSC1)C(=O)NC(C)(C)C)C1=CC=CC=C1 NJBBLOIWMSYVCQ-VZTVMPNDSA-N 0.000 claims description 10
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 10
KRZBCHWVBQOTNZ-RDJMKVHDSA-M (-)-3,5-Dicaffeoyl quinic acid Natural products O([C@@H]1CC(O)(C[C@H](C1O)OC(=O)\C=C\C=1C=C(O)C(O)=CC=1)C([O-])=O)C(=O)\C=C\C1=CC=C(O)C(O)=C1 KRZBCHWVBQOTNZ-RDJMKVHDSA-M 0.000 claims description 9
BHPRDABYBCABNU-NCNGZOBXSA-N (2R)-N-(2-aminoacetyl)-2-[[(2S)-4-[(3-aminophenyl)sulfonyl-(2-methylpropyl)amino]-3-hydroxy-1-phenylbutan-2-yl]-[(3-fluorophenyl)methyl]amino]-3,3-dimethylbutanamide Chemical compound C([C@@H](C(O)CN(CC(C)C)S(=O)(=O)C=1C=C(N)C=CC=1)N(CC=1C=C(F)C=CC=1)[C@@H](C(=O)NC(=O)CN)C(C)(C)C)C1=CC=CC=C1 BHPRDABYBCABNU-NCNGZOBXSA-N 0.000 claims description 9
KRZBCHWVBQOTNZ-RDJMKVHDSA-N (3R,5R)-3,5-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-1,4-dihydroxycyclohexane-1-carboxylic acid Chemical compound O([C@@H]1CC(O)(C[C@H](C1O)OC(=O)\C=C\C=1C=C(O)C(O)=CC=1)C(O)=O)C(=O)\C=C\C1=CC=C(O)C(O)=C1 KRZBCHWVBQOTNZ-RDJMKVHDSA-N 0.000 claims description 9
QRBIFAKBTSNLCS-ZTFBILFISA-N (3S,4aS,8aS)-N-tert-butyl-2-[(2R,3S)-2-hydroxy-3-[[(2R)-3-methyl-3-methylsulfonyl-2-[(2-pyridin-3-yloxyacetyl)amino]butanoyl]amino]-4-phenylbutyl]-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinoline-3-carboxamide Chemical compound C([C@@H]([C@H](O)CN1C[C@H]2CCCC[C@H]2C[C@H]1C(=O)NC(C)(C)C)NC(=O)[C@@H](NC(=O)COC=1C=NC=CC=1)C(C)(C)S(C)(=O)=O)C1=CC=CC=C1 QRBIFAKBTSNLCS-ZTFBILFISA-N 0.000 claims description 9
CUFQBQOBLVLKRF-RZDMPUFOSA-N (4R)-3-[(2S,3S)-2-hydroxy-3-[(3-hydroxy-2-methylbenzoyl)amino]-4-phenylbutanoyl]-5,5-dimethyl-N-[(2-methylphenyl)methyl]-1,3-thiazolidine-4-carboxamide Chemical compound CC1=CC=CC=C1CNC(=O)[C@@H]1C(C)(C)SCN1C(=O)[C@@H](O)[C@@H](NC(=O)C=1C(=C(O)C=CC=1)C)CC1=CC=CC=C1 CUFQBQOBLVLKRF-RZDMPUFOSA-N 0.000 claims description 9
QCNJQJJFXFJVCX-ZDUSSCGKSA-N (4S)-4-(2-cyclopropylethynyl)-5,6-difluoro-4-(trifluoromethyl)-1,3-dihydroquinazolin-2-one Chemical compound C([C@@]1(NC(=O)NC2=CC=C(C(=C21)F)F)C(F)(F)F)#CC1CC1 QCNJQJJFXFJVCX-ZDUSSCGKSA-N 0.000 claims description 9
AMOYMEBHYUTMKJ-UHFFFAOYSA-N 2-(2-phenylethoxy)ethylbenzene Chemical compound C=1C=CC=CC=1CCOCCC1=CC=CC=C1 AMOYMEBHYUTMKJ-UHFFFAOYSA-N 0.000 claims description 9
RTJUXLYUUDBAJN-KVQBGUIXSA-N 2-amino-9-[(2R,4S,5R)-4-fluoro-5-(hydroxymethyl)oxolan-2-yl]-3H-purin-6-one Chemical compound C1=2NC(N)=NC(=O)C=2N=CN1[C@H]1C[C@H](F)[C@@H](CO)O1 RTJUXLYUUDBAJN-KVQBGUIXSA-N 0.000 claims description 9
QRKDOAWSBBGNLE-UHFFFAOYSA-N 2H-1,2,4-benzothiadiazine Chemical class C1=CC=C2N=CNSC2=C1 QRKDOAWSBBGNLE-UHFFFAOYSA-N 0.000 claims description 9
ILAYIAGXTHKHNT-UHFFFAOYSA-N 4-[4-(2,4,6-TRIMETHYL-PHENYLAMINO)-PYRIMIDIN-2-YLAMINO]-BENZONITRILE Chemical compound CC1=CC(C)=CC(C)=C1NC1=CC=NC(NC=2C=CC(=CC=2)C#N)=N1 ILAYIAGXTHKHNT-UHFFFAOYSA-N 0.000 claims description 9
JTEGQNOMFQHVDC-NKWVEPMBSA-N 4-amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-1,2-dihydropyrimidin-2-one Chemical compound O=C1N=C(N)C=CN1[C@H]1O[C@@H](CO)SC1 JTEGQNOMFQHVDC-NKWVEPMBSA-N 0.000 claims description 9
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YMARZQAQMVYCKC-OEMFJLHTSA-N Amprenavir Chemical group C([C@@H]([C@H](O)CN(CC(C)C)S(=O)(=O)C=1C=CC(N)=CC=1)NC(=O)O[C@@H]1COCC1)C1=CC=CC=C1 YMARZQAQMVYCKC-OEMFJLHTSA-N 0.000 claims description 9
MBNNRMVOTYNNIX-HBEKLPNASA-N C(\C=C\C1=CC(O)=C(O)C=C1)(=O)[C@]1(CC(C[C@](C1O)(O)C(\C=C\C1=CC(O)=C(O)C=C1)=O)(C(=O)O)O)O Chemical class C(\C=C\C1=CC(O)=C(O)C=C1)(=O)[C@]1(CC(C[C@](C1O)(O)C(\C=C\C1=CC(O)=C(O)C=C1)=O)(C(=O)O)O)O MBNNRMVOTYNNIX-HBEKLPNASA-N 0.000 claims description 9
NIDRYBLTWYFCFV-FMTVUPSXSA-N Calanolide A Chemical compound C1=CC(C)(C)OC2=C1C(O[C@H](C)[C@@H](C)[C@@H]1O)=C1C1=C2C(CCC)=CC(=O)O1 NIDRYBLTWYFCFV-FMTVUPSXSA-N 0.000 claims description 9
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PYGWGZALEOIKDF-UHFFFAOYSA-N Etravirine Chemical compound CC1=CC(C#N)=CC(C)=C1OC1=NC(NC=2C=CC(=CC=2)C#N)=NC(N)=C1Br PYGWGZALEOIKDF-UHFFFAOYSA-N 0.000 claims description 9
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GSNHKUDZZFZSJB-QYOOZWMWSA-N Maraviroc Chemical compound CC(C)C1=NN=C(C)N1[C@@H]1C[C@H](N2CC[C@H](NC(=O)C3CCC(F)(F)CC3)C=3C=CC=CC=3)CC[C@H]2C1 GSNHKUDZZFZSJB-QYOOZWMWSA-N 0.000 claims description 9
GVZFUVXPTPGOQT-UHFFFAOYSA-M MitoQ Chemical compound CS([O-])(=O)=O.O=C1C(OC)=C(OC)C(=O)C(CCCCCCCCCC[P+](C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1C GVZFUVXPTPGOQT-UHFFFAOYSA-M 0.000 claims description 9
229950008798 Mozenavir Drugs 0.000 claims description 9
229960000689 Nevirapine Drugs 0.000 claims description 9
NQDJXKOVJZTUJA-UHFFFAOYSA-N Nevirapine Chemical compound C12=NC=CC=C2C(=O)NC=2C(C)=CC=NC=2N1C1CC1 NQDJXKOVJZTUJA-UHFFFAOYSA-N 0.000 claims description 9
REFJWTPEDVJJIY-UHFFFAOYSA-N Quercetin Chemical compound C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC=C(O)C(O)=C1 REFJWTPEDVJJIY-UHFFFAOYSA-N 0.000 claims description 9
229960001285 Quercetin Drugs 0.000 claims description 9
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XNKLLVCARDGLGL-JGVFFNPUSA-N Stavudine Chemical compound O=C1NC(=O)C(C)=CN1[C@H]1C=C[C@@H](CO)O1 XNKLLVCARDGLGL-JGVFFNPUSA-N 0.000 claims description 9
229960002555 Zidovudine Drugs 0.000 claims description 9
HBOMLICNUCNMMY-XLPZGREQSA-N Zidovudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 HBOMLICNUCNMMY-XLPZGREQSA-N 0.000 claims description 9
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JP2009518393A 2006-07-07 2007-07-06 治療薬の薬物動態の調整 Active JP4881433B2 (ja)